Chloronitroparaffins as insecticides



. propane, tri(chloromethyl) Patented July 14 1942 nvites STATES PATENT FFIE ontono mrnorsnarrms as iNsEc'rrcInns Hans Z. Lecher and Asa Willard Joyce, ilainfield,

N. 3., assignors pany, New York,

No Drawing.

4 Claims.

This invention relates to insecticides and is concerned more particularly with a class of compounds adapted to the fumigation of enclosed spaces for the eradication of insects and allied Pests.

We-have discovered that valuable insecticidal properties are exhibited by the class of chloronitroparaflins oi the general formula are selected from the group radical. Typical examples of such compounds include 1-chloro-2-nitroethane, 1-chloro-2-nitroto iilymerican Cy Application August 23, 1940, Serial No. 353,916

anamid Com,- a corporation of Maine propane, 1-chloro-2-nitrobutane, 1-chloro-2-ni-.

EXAMPLE 1 Preparation of 1-chZ0ro-2-nitrobutane.39.7 parts (0.33 mole) of 2-nitro-1-butanol are dissolved in 31.6 parts (0.4 mole) of pyridine in a vessel equipped with stirrer, "thermometer, reflux condenser and dropping funnel. 47.6 parts (0.4 mole) of thionyl chloride are dropped in slowly while agitating the mixture. The temper- :ontinued for 3 hours, the mixture is cooled and tdded to 200 parts of water. A dark heavy oil vhich separates is washed with aqueous soda soution. Carbon tetrachloride is istilled under reduced pressure. aving a pungent odor is obtained as a fraction te oiling at 76-79 C. under a vacuum of about 14 55 lulcsic board, cloth and in Example 2. The product is obtained in very good yield and hasa boiling point of 92-990. at

with others, is applied as yl propanol are EXAMPLE 2 Preparation of I-chloni-Z-nitro--methyl proof 2-nitro-2-methpane.4 5.0 parts (0.378 mole) dissolved in 31.6 parts (0.4 mole) of pyridine in a vessel equipped as in Example 1. 59.5 parts (0.5 moleioi thionyl chloride are add ed slowly to the mixture, the temperature rising C. The reaction mixture is then heated to -95" C. for 3 to 600 parts of water. A

propane is collected in good yield as boiling at 68-69 The reaction one hour at 50 0., followed by refluxing at C. for 2 hours. After cooling to room'temperature, 250 parts of water are added. The chloro derivative separates as a crystalline substance. It is filtered, washed with cold water, and recrystallized from alcohol. M. P. 100-10210.

e fumigant, either alone or in admixture for example by atomizing or vaporizing with or without heat into the The invention will be illustrated in greater dehours. cooled Fumidcm-t: l-chloro -2-nitro-2-methvl propane I Insect Dosage Exposure Kill int 7 Hours Percent9 i weevil 4 mg. or R Do 8 mg.,'liter 4 98 we rt; t 2i 2% k t beet e rvaemg.

o 12 mgJliter 24 70- Olothes moth larvae Seturatedvapoxs. 24 60 TABLE III 'Fumigant: 1,3-dichloro-Z-nitro-Z-methyl propane Insect Dosage Exposure Kill I M Hours Percent Rice weevil Saturatedvapors. 2 a 82 Do do--- 4 98 Do do 24 100 Confused flour beetle do 4 81 Do -do-- 24 100 Black carpet beetle larvae" ..do 24 100 Clothes moth larvae 4mg.lli 4 -80 Do Saturated vapors. 4 100 performed on vari- Y erties.

TABLE IV Fumigcnt: trflcltloromethul) -nitromethane In the above tables where the dosage indicated issaturated vapors, it is to be understood that the air in the fumigation vessel was saturated with the vapors or the Iumigant.

From the above it is concluded that the entire class of chloronitroparafiins oi the general formula set out exhibit valuable insecticidal propinvention has been described with particular reference to specific embodiments,- it is to be understood that it is not to be limited thereto but is to be construed broadly and restricted solely by the scope of the appended claims. 7

Weclaim: K

1. An insecticide including an effective amount of a compound of the general formula While the NO: R JJ-CHrCi an alkyl radical consix carbon atoms,

HANS -z. LECHER. ASA WILLARD JOYCE.

are selected from the group I and the CH2C1 

